Bart Simpson: Teenage Wasteland
by Frostbittenpleasure007
Summary: Bart Simpson was your average, underachieving middle school student, until one day he starts to notice the wonders of girls Characters 2 years older Bart X Nikki. And Eventual Nelson x Lisa and other couples maybe Don't Like Don't Read, will be sexual I Do Not Own The Simpsons, All Characters are owned by 20th Century Fox and Matt Groening.
1. Growing Up Simpson

Bart Simpson was your average under-achieving middle school student he got below average grades. He had friends who worshiped the ground he walked upon, he had a sidekick who waited upon his beck and call. And was clearly the coolest boy in Springfield Middle School. Unfortunately, when Bart left Springfield Elementary, Principal Skinner moved with him as Superintendent Chalmers could not find a suitable replacement for the old principal, who just happened to be Sideshow Bob for some reason. But even so he didn't change a lot since elementary school. but there was one tiny change.

He was going through puberty, and as a result he was feeling all these weird new feelings. But his worst problem was his constant state of arousal. Every morning he would wake up to a painful boner, and he didn't know why. And it was starting to worry him. Bart had to search these things himself on the internet because, as usual, his dad Homer, was of little assistance. Recently Bart had discovered Masturbation by accident when his ex-girlfriend Nikki McKenna sent him a picture of her in a skimpy bikini, Bart was gonna shut his phone off, until he realized he was getting that annoying feeling of arousal he was used to, so he decided that maybe Nikki would be his focus for his next jerk off session.

So Bart got into his bed and pulled of his shorts, and underwear and took out his dick he started to picture Nikki and him kissing on a sandy beach while she stripped off her sexy little bikini. What with Bart being so inexperienced he quickly shot 3 sticky ropes of cum onto his belly.

"Aye Caramba!" said Bart as he lay there panting, and shaking from his mind blowing orgasm. He decided he would have to talk to Nikki and convince her to go out with him again, so maybe just maybe he could see her naked for real.

All that week during school, Bart was constantly flirting with her, and most of the toime he would have to go wank in the bathroom afterwards. Shooting wads of cum against a pair of her panties he stole from her gym bag.

Eventually she agreed to officially say they were dating, so that Friday, Bart and Nikki went to the movies, and saw Sever VI, which Bart and Nikki had both already seen, the reason for going of course was so they could fool around the entire time. At one point Nikki starting grinding against Bart's lap and he got a boner, she lifted up her skirt and showed him how wet she was. Bart decided to leave the movie with Nikki so they could go make out in one of the most popular spots for young teens for who were horny as fuck.

They went to the playground and made out inside the tube slide, Nikki told Bart that even though she was only 12 she wanted to make love to him. So Bart started by taking out his dick, Nikki wrapped a tiny, girly hand around Bart's shaft and jerked him, she needed no instruction on how to give the perfect handjob, she decided to tease him, so she took her hand away right as he was about to blow.

Feeling rejected, Bart gave her puppy dog eyes which quickly turned into the drooling and panting of a bulldog. Nikki took off her shirt and training bra and let Bart touch her boobs. She then took Bart's schlong into her mouth and sucked him off.

"Nikki, I'm gonna cum!" said Bart.

"Not yet you loser." said Nikki looking at Bart like she dared him to jump off a cliff.

"Too bad babe, this ship has sailed, I'M CUMMING!" shouted Bart as he shot load after load of sticky white gold onto Nikki's face and chest.

Bart knew what was next, he made Nikki lie down as he pulled off her panties. He slowly stroked her clit with his thumb and licked her wet folds with his tongue.

"Bart baby FUCK ME!" moaned Nikki as she seized up and her eyes rolled into the back of her head as she orgasmed.

"WHOA MAMA!" exclaimed Bart as Nikki's sweet, creamy girl goo squirted out into his mouth.

Laying there spooning her fragile half naked body, he decided he was too tired to fuck her, so they got dressed and went home. Bart asked if she wanted to fuck for real soon, and she said she would love that.

Bart Simpson, Age 12, 6th Grade just got some action, and he couldn't wait until he scored again


	2. Morning Wood Removal

As mentioned in the description i don't own the simpsons, i just like to write stories about them

Chapter 2:

Bart's head was still spinning from the night before when he woke up, last night he got to 3rd base with his girlfriend Nikki McKenna, and he could still faintly taste her juices on his lips. He couldn't wait to see her again, in fact he had ended up pitching a tent thinking about her. But rather than take care of it himself, he texted Nikki and asked if she wanted to go out to the old abandoned playground and fool around, she said she would meet him there in 15 minutes.

When Bart got to the playground he found a scantily clad Nikki waiting for him in the sandbox. "Wait babe, we should move, I don't want to get sand up inside me, plus who knows how many cats or children have pissed in this thing." Bart laughed and grabbed her ass as they ran to the tube slide again. She took of her shirt and showed him she wasn't wearing a bra. Bart immediately started licking her nipples. "MMM OH FUCK!" Nikki squealed. And she started rubbing herself. Bart took out his cock and started tittyfucking her, slipping his cock through what little titflesh a girl her age had, but suffice it to say, he thoroughly enjoyed himself nonetheless. She then took his cock into her mouth and sucked him near orgasm, and spit it out before he blew his wad. Bart asked her why and she asked him to eat her out, grudgingly Bart licked her delicious pussy. "Mmmmmmm Dammit Honey, Make me squirm." sighed Nikki. "Your wish is my command angel." said Bart in a sexy tone. "AHHH FUCK!" screamed Nikki as she released her juices on Bart's face. "Hey why do you get to cum, and I don't?" whined Bart. "Because you're gonna fuck my pussy stupid." explained Nikki.

Bart took his dick and lined himself with Nikki's hot, slippery, pink pussy and pushed the head in. "MMMPH It hurts!" cried Nikki, sniffling like a baby. "Don't worry baby, it'll feel great once i'm in." explained Bart reassuringly. He shushed her and coddled her like a baby, and then asked if he could continue, she said yes. He pushed his dick further in and waited until her pain subsided. Bart wasn't incapable of feeling compassion or apathy, he just selectively used for people that mattered. In which case Nikki realized she was very special. He finally started thrusting in and out, and Nikki started moaning. "Oh my goooooooood, you feel greeeeeat!" sighed Nikki. "You too baby, you're so damn tight." Bart said between thrusts and grunts. Soon enough the preteen lovers hit their peaks, and came together in a loud, sweaty mess. They laid there spooning for about a half hour, and then said goodbye, and returned to their respective homes.

When Bart returned, his sister Lisa asked where he had been, when he just mumbled instead of answering, she knew something was up, and she would find out or her name wasn't Lisa Marie Simpson. She smelled something on Bart, it smelled like perfume and sweat. It was then that Lisa realized Bart had been having sex with a girl. Normally Lisa would rat her brother out, but she though better of it, since she didn't want bart doing the same thing to her, since he knew about her secret relationship with one Nelson Mandela Muntz.

**Lisa's Flashback:**

"Oh, Nelson how could I resist you, I never did stop loving you." said Lisa as she gazed lovingly into those eyes, those eyes that made her forget all her problems, who thought they would belong to Nelson Muntz. Sure they had dated in the past, but they were just kids, now they were older and it seemed like it would last. however it would have to be kept a secret as Marge didn't want Lisa dating him, she had been promoting Milhouse, but that seemed unlikely, I mean come on Milhouse? Really?

She and Nelson had been having sex in his house, because his mom couldn't have cared less about who or what was there. So it was easy to make love with him. Bart however found out quite easily, through Jimbo, Dolph and Kearney, who told him in exchange for a pair of his mom's panties. So Bart could easily pull out the blackmail card should he choose to.

One afternoon, Lisa and Nelson were fucking, "Oh Nelson you're soooooooo big, i love it!" squealed Lisa. "yeah i know, HA HA." Nelson grunted, finishing it off with his trademark laugh. "God I love when you laugh." Lisa moaned. "Well, that's not hard to use, glad I found a turn on for ya, HA HA HAAAAAAAAAAAAAAA!" Nelson said as he came in Lisa triggering her orgasm. "AHHHH NELSON FUUUUUUUUUUUUUUUUUUCK!" screamed Lisa, when just then Bart burst in through the door. "Ah Bart get out i'm naked." screamed Lisa. "Not so fast Leese," said Bart, "If you don't do what I say i swear to god i'll tell mom you and nelson are together, and fucking no less." "FINE BART! You win, but if i find anything on you that mom won't like, i won't play as easily." said Lisa defeated.

**END FLASHBACK:**

And now she had her blackmail.

So guys how was that, I say this assuming some people have at least skimmed my story. Reviews are always nice, and I hope you enjoyed this, what will this Lisa x Nelson Storyline add, well i guess you'll have to wait and see.

See ya,

Frost


	3. Payback, Sexuality and Mindfucking OH MY

As always I do not own the simpsons

Chapter 3:

Bart and Nikki, were up in the treehouse listening to some music on Bart's Ipod, when suddenly, Soul to Squeeze by The Red Hot Chili Peppers comes on. (_**Authors Note: You might want listen to the song, i find reading and listening to a corresponding adds to effect but whatever you choose is coo**_l) "Mmm babe I want to squeeze your soul, and by your soul I mean your boobs." said Bart seductively. "Well come over here lover boy" said Nikki grinning. And with that the shirts and pants came off, and the groping commenced.

"Ahh how I love to suckle your tits my lady." said Bart with a sort of british accent. "Well I do believe I wish to caress your balls, sir" responded Nikki in a similar snarky tone. "whatever you say babe." said Bart taking off his boxers. "WAIT! Do it sexily." Nikki growled with lust. "Gimme some tunes babydoll." said Bart. So Nikki hits shuffle, and what else should come on but My Humps by The Black Eyed Peas. "I don't know how that got on there!" Bart stammered. "Uh uh uh, Shut up Bitch and dance for my arousal, I want to see that ass twerking." purred Nikki. So Bart did as he was told, and afterward, Nikki literally knocked him out of the treehouse window, and they started to roll around on the ground, naked. "It seems Homer isn't the only one who can go nude in the backyard." said Lisa snapping pics with her camera, it was time for some revenge, and this was just too perfect.

Bart had taken his blackmailing abuse a bit too far, when he told Lisa, to masturbate in public in front of the entire school on the playground, of course Lisa didn't have much of a choice. However she did buy herself a bit of time so she could dig up some dirt on Bart. She used some lame excuse like, "Bart, I can't I'm on my period." Which Bart completely bought, and she had at least a week to get something on Bart.

Eventually the day came when Lisa had to finger herself in public, and she decided that she would play it up a bit. So as she laid back on the teeter totter preparing to expose her pussy to the entire playground, she pulled a set of pictures out of her thong and showed them to Bart. Bart's face dropped, and his mouth was gaping. He decided to call off the whole thing, and he told Lisa that there would be no further blackmailing on the subject. So now the two romances could flourish freely, well that was before Nelson cheated on Lisa with Sherri and Terri.

So now Lisa was alone, and she was desperate, and horny. She even considered hooking up with Milhouse, but then she realized and said "Why does it have to be a boy, girls are just as hot." So she called up a girl, who she knew would drive Bart insane if he saw her with Lisa. She wanted to take care of the fire between her thighs and screw with her brother's spiky little head.

The doorbell rang, and Bart, expecting Nikki, went to get it. But when he opened the door, there stood his stunning ex-girlfriend, Jessica Lovejoy. "Jessica what are you doing here?" asked Bart "I'm with Nikki, you're too late to hook up with me." "I know that you idiot, I'm here to have a um, uh...Playdate with your sister." stuttered Jessica while Blushing. "Okay, whatever man." said Bart. Clueless as always thought Jessica. "Leese, Jessica Lovejoy's here." said Bart

So guys sorry but imma stop here to keep you hooked, the reason for this was because i always saw lisa as either Bi or Lesbian, so i thought i'd add a little plot twist. Also, I try to combine sex and comedy in this, so I hope that's working

Also a little side note, I plan on starting another story probably for something like Jessie or Sam and Cat, or something like that, so ya know check it out when it goes up

Frost


	4. Extreme Days, and Kinky Nights

Hey everyone, sorry for the delay, I was away this weekend, and then y'know writers block and stuff. But after spending some time looking at simpsons stuff on Rule 34, some of this may seem a little crude, because i really was gonna go all out, so go away if u don't like it. so here we go

I DON'T OWN THE SIMPSONS

Lisa and Jessica were in her room, both were naked on her bed, making out, Jessica had her fingers jammed in Lisa's pussy, while Lisa's toes were in Jessica's pussy. "Oh my god, this is fantastic" said Lisa. "I know right, let's cum together" moaned Jessica, as the two squirted their juices against each others pussies. Both girls were barely satisfied, so they went at it again, meanwhile Bart had witnessed the entire thing through his peephole in the bathroom. So he laid there rolling around on the shag carpet, jizzing all over his belly, and his fingers in his butt, a trick Milhouse had shown him. "Holy shit that was fucking amazing, I need to fuck Nikki NOW" moaned Bart. So he cleaned up and texted Nikki, to meet him down at the playground, on his way, he grabbed his skateboard, he had something kinky in mind.

When he got to the playground he saw Nikki, and told her to get on his skateboard on her belly with just her panties on. She did as she was told, and before she could relax, Bart came up behind her, and starting humping her, her panties ripped, and a hole opened up right over her pussy, as Bart begin to thrust. "Oh Bart FUCK ME HARD!" screamed Nikki. And the couple continued to fuck on skateboards for the rest of the day, when they finished, Bart's skateboard was encrusted with dried cum and vaginal fluids. He then headed for home, where he watched Jessica and Lisa, fucking each others pussies, cumming thrice. before calling Milhouse over, the 2 boys sat and jerked their cocks, until they passed out from the pleasure.

Lisa and Jessica walked to her house, as they passed an adult store, which they knew was notorious for selling sex paraphernalia to minors. They purchased, Pussy Pumps, Double Dildoes, and tons of lube, to enhance the experience they were going to have at Jessica's house while her parents were away. But when they got naked, Jessica stepped out for a minute, and when she came back, she was wearing a diaper, and she had one for Lisa. The two girls wore the diapers and mashed against each other, shtting and pissing and cumming, and both girls went through a pack of diapers that night, both waking up wet the next morning, in more ways than one.

Bart and Milhouse were having a sleepover that night and Homer and Marge were out, the two boys were alone, and so they ran around naked and watched porn all night, jacking each other off, and sucking each others cocks. Bart and Milhouse were extremely into it, and though Bart was with Nikki, nobody knew about the boy's secret, and nobody ever would.

Bart came all over Milhouse's face and vice versa before the the two friends fell asleep, and it was a long night's sleep interrupted by the natural phenomena of morning wood that both Boys were sporting.

So That's that, I don't know if that was good or bad, but thats that i suppose, i'll update eventually

frost


	5. Rain Keeps Falling Down

Hey everybody, I've been gone so i could actually give this fic some plot, but it was tough, but i think you might like what i came up with. note that this chapter will be slightly less sexual as i am setting up future storyline ideas.

I DON'T OWN THE SIMPSONS 

Bart and Milhouse woke up hours later, in a post orgasmic haze. Milhouse started to jerk off again, but Bart said he had other plans. Milhouse knew he was going to see Nikki, and that his only chance was now. You see after some serious thought after his last rejection by Lisa, he realized, he wasn't interested in chasing her anymore, it's not like she was the one who Milhouse depended on most, who he trusts his life and safety with. And that's when it hit him, his attraction was to not Lisa Simpson, but Bart Simpson, his best friend.

"Bart there's something I have to tell you, but i'm kinda embarrassed and worried you won't like it." said Milhouse worriedly. "Milhouse you're standing next to me naked covered in your own jizz mixed with mine, after we spooned while tired and came in front of eachother, I think you can tell me something without being embarrassed." Bart reassured him sarcastically. "Well okay," he started, "Bart, I love you and I want you to break up with Nikki and be with me." Milhouse, I never thought I would ever see you in a more pathetic state than you are now. I can't be with you, what we do is as friends." Bart scolded him. "WELL HOW THE FUCK WAS I SUPPOSED TO KNOW SIMPSON, I THOUGHT YOU RECIPROCATED MY FEELINGS YOU BASTARD!" screamed Milhouse. "Milhouse, I think you should leave and not talk to me for awhile, I can't see you right now." said Bart with tears in his eyes. "Milhouse I don't want to send you away, but I can't have you here accusing me like this, Nikki is my heart and soul, and I won't leave her, and if you can't acceot our relationship then just GET THE FUCK OUT!" he finished sobs, wracking his frame.

Bart layed in bed sobbing all day, because he knew that was it, Milhouse wouldn't come back unless Bart went gay for him, and he couldn't do that full time, he was just a kid who liked experimenting, he wasn't making decisions like that yet. When he told Nikki his problems, she told him that he was right in his decisions, and that she was glad he chose her, but then her bi-polarity snapped to attention. "WAIT YOU EXPERIMENTED WITH A DUDE, WHILE YOU WERE DATING ME WHAT THE FUCK BART?" she screamed. "Wait Nikki, don't do this to me, in the end I chose you that's all that matters. "NO IT'S NOT ENOUGH I'M FUCKING DONE WITH YOU, I'M BREAKING UP WITH YOU ASSHOLE!" shrieked Nikki. "NIKKI PLEASE DON'T LEAVE I'LL MAKE IT UP TO YOU PLEASE BABY!" Bart wailed, banging his fists on the ground, grabbing her leg dramatically. But it was too late she was gone.

Bart was hanging out with Nelson and the bullies, sympathizing with him, of course Bart told them an altered form of the story, so the details about Milhouse were skipped. It was then that Bart changed his life for the worse, Jimbo offered him a small pill, and told him it was called acid and that it would make all his problems vanish into a puddle of colors. And so it began, Bart Simpson's downward spiral into the colorful but not so glamourous world of LSD.

So, how was that, the story is called Teenage Wasteland after all, so you had to expect this eventually right, though it seems it is over the story has only begun, hope you guys stick around Frost :)


	6. This Is My Last Resort

Hey, everyone, sorry it's been so long, but towards the end of summer break, i kinda lost my spark, then school started, and i was swamped in work, as it is i'm currently doing a 5 page report on pink floyd for my music appreciation class, (which to be honest really isn't a problem, i love music, so a report or powerpoint, really not a problem) but i suppose that's not important, on with the story then

WARNING: This is going to be EXTREMELY descreptive in terms of his acid trips, I only write from experience and hope you don't blame me for any images being burned into your minds.

As always, I DO NOT OWN THE SIMPSONS!

Bart woke up in a puddle of vomit next to his bed, he came home tripping hard, when Lisa found him, she didn't want Homer or Marge to see him like this, so she dragged him up to his bed, and stayed with him for awhile. She wondered what could convince him to sink so low he would abuse his body like this. Then she saw the note stuffed in his jacket, about what happened, written in barely legible writing was the following:

My dearest Nikki, Without you I feel an emptiness the equivalent of a black hole, though all i can see is rainbows, i truly see the blackness in my soul that you have left me with, I truly deserve everything that's coming to me, and i hope i fucking die. as long as i can't have you, i deserve nothing, let my body rot in a cell, my brain melt and collapse within the mighty colors of the acid queen, and my heart eat itself withtin the blackened core of my being.

Sincerely,

Bartholomew Jojo Simpson

Lisa layered there weeping for her brother, she had never read anything so sad, she had no idea, how deeply he cared for Nikki, she had to help him, because she knew if she didn't he'd go out, drop acid and most likely kill himself.

Bart met up with the bullies again, and dropped acid and snorted cocaine, the mix of uppers and downers, screwed with his system so badly he was in bed for 5 days afterward, being haunted by dreams of an altered reality,

In one dream, he was falling out of the mouth of an angry zombie clown, blood gushing from his eyesockets and spiders bursting out from his skin, maggots ate out of the wounds, and turned to flies leaving his mutilated corpse in a pool of black tar-like blood that gushed from his wounds.

In another, he was looking at himself in a mirror, when Milhouse and Nikki, both grabbed his body and ripped him limb from limn, only to let scorpions and fire ants eat his cartilage and flesh, while he lay the bleeding rainbows and nuclear waste, as Mr. Burns laughed Maniacally ver his dying frame.

When he finally awoke, he drank a full bottle of nyquil just to go back to sleep, so he wouldn't have to fell anymore.

So, i'm really sorry that was so graphic you guyd, but i wanted to start of with a dramatic return to the site, by the way, i do partake in the use of recreational drugs like weed and acid, and i DO NOT promote them in anyway, they are a dangerous thing to use, and i do not want my readers thinking i am glorifying them, if anything i'm scaring you guys shit;ess, because trust me, this chapter, may or may not be be based on a personal experience. Sorry, don't judge me by my actions please?

Frost ;)


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